Hydrochloric Acid → HCID 178490727, compound

HRID 989544Notes

Reaction equation

HRID 989544 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([S:8]([O:11][C:12]2[CH:13]=[C:14]([CH:24]=[C:25]([CH3:27])[CH:26]=2)[O:15][CH2:16][CH2:17][CH2:18][O:19][NH:20][C:21]([NH2:23])=[NH:22])(=[O:10])=[O:9])[CH:7]=1.C(OCC)C.Cl>CC(O)C.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([S:8]([O:11][C:12]2[CH:13]=[C:14]([CH:24]=[C:25]([CH3:27])[CH:26]=2)[O:15][CH2:16][CH2:17][CH2:18][O:19][NH:20][C:21]([NH2:23])=[NH:22])(=[O:9])=[O:10])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 178490726HCID 178490726, compound

Product 1

HCID 178490727HCID 178490727, compoundYield 201.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

The hydrochloride salt of the title compound was made by adding a solution of the free base, 3-[3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyguanidine, (261 mg, 0.59 mmol) in 2-propanol (6 mL) to diethyl ether (100 mL) containing HCl in ethanol (1.1 mL of a 1.1 M solution, 1.2 mmol). Solvent was removed in vacuo to give the title compound (285 mg) as a colorless oil. 1H-NMR (300 MHz, DMSO-d6)(7.86 (dd, 1H, J=9.0, 2.7 Hz), 7.65 (d, 1H, J=2.7 Hz), 7.44 (d, 1H, J=9.0 Hz), 6.74 (br s, 1H), 6.49 (br s, 1H), 6.43 (br s, 1H), 4.01 (s, 3H), 4.00 (t, 2H, J=6.4 Hz), 3.91 (t, 2H, J=6.3 Hz), 2.23 (s, 3H), 2.02 (pentet, 2H, J=6.3 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H22ClN3O6S: 444.1 (M+H). Found 443.5.

Workup

  1. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-7660aaecb43c418dab1a0024fa14e3af
Source dataset
uspto-grants-2003_10
Patent number
US06638931B1

Reaction notes

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